Biphenyl compounds useful as muscarinic receptor antagonists

1. A compound of formula XVIII:

wherein:

a is 0 or an integer of from 1 to 5;

each R 1 is independently selected from (1-4C)alkyl, (2-4C)alkenyl, (2-4C)alkynyl, (3-6C)cycloalkyl, cyano, halo, —OR 1a , C(O)OR 1b , —SR 1c , —S(O)R 1d , —S(O) 2 R 1e , —NR 1f R 1g , —NR 1h S(O) 2 R 1i , and —NR 1j C(O)R ik ; where each of R 1a , R 1b , R 1c , R 1d , R 1e , R 1f , R 1g , R 1h , R 1i , R 1j , and R 1k is independently hydrogen, (1-4C)alkyl or phenyl(1-4C)alkyl;

b is 0 or an integer of from 1 to 4;

each R 2 is independently selected from (1-4C)alkyl, (2-4C)alkenyl, (2-4C)alkynyl, (3-6C)cycloalkyl, cyano, halo, —OR 2a , —C(O)OR 2b , —SR 2c , —S(O)R 2d , —S(O) 2 R 2c , —NR 2f R 2g , —NR 2h S(O) 2 R 2i , and —NR 2j C(O)R 2k ; where each of R 2a , R 2b , R 2c , R 2d , R 2e , R 2f , R 2g , R 2h , R 2i , R 2j , and R 2k is independently hydrogen, (1-4C)alkyl or phenyl(1-4C)alkyl;

W represents O or NW a , where W a is hydrogen or (1-4C)alkyl;

c is 0 or an integer from 1 to 5;

each R 3 independently represents (1-4C)alkyl or two R 3 groups are joined to form (1-3C)alkylene, (2-3C)alkenylene or oxiran-2,3-diyl;

m is 0 or 1;

R 4 is selected from hydrogen, (1-4C)alkyl, and (3-4C)cycloalkyl;

s is 0, 1 or 2;

Ar 1 represents a phenylene group or a (3-5C)heteroarylene group containing 1 or 2 heteroatoms independently selected from oxygen, nitrogen, and sulfur; wherein the phenylene or heteroarylene group is substituted with (R 5 ) q where q is 0 or an integer from 1 to 4 and each R 5 is independently selected from halo, hydroxy, (1-4C)alkyl, and (1-4C)alkoxy;

t is 0, 1 or 2;

n is 0 or an integer from 1 to 3;

d is 0 or an integer from 1 to 4;

each R 6 independently represents fluoro or (1-4C)alkyl;

p is 0 or 1; and

R′ is selected from hydrogen, —CH 3 , and —CH 2 CH 3 ;

wherein each alkyl and alkoxy group in R 1 , R 1a-1k , R 2 , R 2a-2k , R 3 , R 5 , and R 6 is optionally substituted with 1 to 5 fluoro substituents;

or a pharmaceutically acceptable salt or stereoisomer thereof.

2. The compound of claim 1 , wherein a, b and c each represent 0.

3. The compound of claim 1 , wherein W represents O.

4. The compound of claim 1 , wherein m is 0, s is 0 and t is 1.

5. The compound of claim 1 , wherein the —COOR′ group is in the para position, d is 0 and n is 2.

6. The compound of claim 1 , wherein Ar 1 represents phen-1,3-ylene, phen-1,4-ylene, 2,4-thienylene or 2,5-thienylene; wherein the phenylene or thienylene group is optionally substituted with one or two R 5 substituents.

7. The compound of claim 6 , wherein Ar 1 represents phen-1,4-ylene or 2,4-thienylene, optionally substituted with one or two R 5 substituents.

8. The compound of claim 1 , wherein R 4 is selected from hydrogen, methyl and ethyl.

9. The compound of claim 1 wherein a, b and c each represent 0; W represents O; m is 0; s is 0; t is 1; Ar 1 represents phen-1,4-ylene optionally substituted with one or two R 5 substituents; d is 0; n is 2; and the —COOR′ group is in the para position.

10. The compound of claim 9 , wherein R 5 is independently selected from halo, (1-4C)alkyl, and (1-4C)alkoxy, wherein each alkyl and alkoxy group is optionally substituted with from 1 to 3 fluoro substituents.

11. The compound of claim 9 , wherein R′ is hydrogen.

12. The compound of claim 9 , wherein R′ is —CH 3 .

13. The compound of claim 9 , wherein R′ is —CH 2 CH 3 .